An asymmetric catalyst is used for deriving an asymmetric compound from a compound having no asymmetric carbon by a chemical synthesis.
As it is disclosed in Marc Lemaire et al., Chemical Reviews 105, p 1801-1836 (2005) and in J. P. Genet et al., Tetrahedron Asymmetry, 5(4), p 675-690 (1994), a bis(diphenylphosphino)binaphthyl compound is known as a catalyst having excellent asymmetric induction ability. A method using such compound for industrially mass-manufacturing an asymmetric compound such as l-menthol with high optical purity and in a high yield is also known. However, as Marc Lemaire et al. discloses, it is very difficult to chemically modify the bis(diphenylphosphino)binaphthyl compound of low reactivity to synthesize a derivative thereof in a high yield through short steps. Moreover, after using the derivative as a catalyst, it is necessary to recover the catalyst after the reaction through troublesome procedures. Furthermore, the catalyst cannot be recycled in spite of its expensiveness.
Albert S. C. Chan et al., Journal of American Chemical Society, 121, p 7407-7408 (1999), Tamio Hayashi et al., Organic Letters, 6(19), p 3357-3359 (2004), D. J. Bayston, The Journal of Organic Chemistry, 63, p 3137-3140 (1998), Christine Saluzzo et al., Bioorganic & Medicinal Chemistry Letters, 12, p 1841-1844 (2002), and Japanese Patent Provisional Publication No. 2004-161963 disclose polymers having bis(diphenylphosphino)binaphthyl groups that can be simply recovered. Generally, such polymers are synthesized through complicated multiple procedures, and an overall yield or an asymmetric yield thereof may be low, or the sort of the resin in the polymer may be limited. Therefore, using such polymers is inconvenient,
The inventors of the present invention found that from a dioxide derivative of the bis(diphenylphosphino)binaphthyl compound disclosed in Toyoshi Shimada et al., The Journal of Organic Chemistry, 66, p 8854-8858 (2001), a 5,5′-diiodide can be derived in a high yield by a method disclosed in Toyoshi Shimada et al., The Journal of Organic Chemistry, 70, p 10178-10181 (2005).